Mission Possible?
by sheltie
Summary: Advanceshipping one-shot. Ash and May are over eighteen in this one.


**Mission Possible?**

**By: Sheltie**

_I don't own Pokémon at all_

Cerulean City gym leader Misty Waterflower sighed as she entered the restaurant. She took off her shades and looked around hoping to spot her friend.

"Misty, over here!"

Misty spotted her, it was hard to overlook as the girl was waving her hands about frantically. The orange haired girl felt her cheeks redden with embarrassment as she made her way over.

"Hey Dawn" Misty said

"Hi Misty, I'm so glad you could come" Dawn said

"You said that it was important and that it was something to do with Ash" Misty said

"It is, it is very serious Misty" Dawn said in a serious tone

Misty braced herself for the worst.

"I need your help getting Ash to realize his feeling for May" Dawn said

Out of everything Misty thought the blue haired girl would say this was definitely not on the list.

"WHAT!"

This got the attention of most of the restaurant. Misty ducked her head in embarrassment. The two girls waited until everything went back to normal to continue their talk.

"What makes you think I'd help you with this?" Misty hissed

"You know Ash the best, well other than Brock, but you know that asking Brock for advice would not be a great idea" Dawn said

Misty had to agree with this. The former Pewter City gym leader and now Pokémon breeder was never good at all giving love advice. She remembered when her boyfriend Tracey went to Brock for advice. Lets just say that it was the corniest anniversary ever.

"Fine, but how do you even know that Ash likes May that way?" Misty asked

"Well first we need confirmation that Ash has feelings for May, but you know how dense Ash is" Dawn said

Misty nodded, she was quite aware how dense her best friend could be.

"So I need you're help with that, I was thinking that if we double team him he'd crack" Dawn said

Misty blinked, this was the girl's plan?

"How do you know that it will work?" Misty asked

"Don't know if it will, but you'll never know unless you try" Dawn said with confidence

Misty sighed and agreed, knowing she'd probably regret it later.

Ash Ketchum, aspiring Pokémon trainer sighed as he laid his head back. He was in his backyard resting after his journey through the Sinnoh region. He decided to take a bit of a break since he's been going non-stop since he began as a trainer. So that's why he was home lying in his backyard enjoying some peace and quiet.

"Hey Ash!"

Ash groaned, only one person could break his peace right now. He looked up to find Dawn waving at him in an excited manner. Dawn traveled with him when he was in the Sinnoh region. She was an energetic Pokémon coordinator, who is following in her mother's footsteps as a coordinator. He liked the girl well enough, but she could be rather annoying at times, which is what Ash thought what a little sister might be like if he had one.

"What is it Dawn?" Ash asked

"Nothing really, well can we talk?" Dawn asked

"Sure, what is it you want to talk about?" Ash asked now sitting up

"Well, um, I'm not how to say this, but I have a crush on someone" Dawn said nervously

"Y-you do" Ash said not liking where this was going

"Yeah, and I was wondering if you could help me get him to notice me" Dawn said

Ash scratched the back of his head. He had no clue why Dawn would ask his help on this problem. He didn't have a girlfriend let alone knew anything about girls.

"Uh Dawn, do you really think that I'm the best person to talk to. I mean, May would be better and even Misty could help you" Ash said

"Did someone say my name?"

Ash shifted his head and saw that one of his oldest friends walking in.

"Hey Mist" Ash greeted

"Hey Ash, so what's up?" Misty asked

Dawn told Misty her problem and Ash got up to leave.

"Where are you going Ash?" Misty asked

"Well I thought since you're here that you could help Dawn since I can't help her at all" Ash said

"Sit down Ketchum" Misty ordered

Ash plopped back down to the ground with a sigh. He had no way out. So He had to endure Misty and Dawn's talk. He felt his lids get heavy, but fought to stay awake since he didn't want to feel Misty's wrath. As he listened his mind began to wander.

"So Ash, do you have a crush on someone?" Dawn asked

This question woke Ash up.

"What?"

"Dawn asked if you had a crush on someone" Misty said

"Oh, um, well, I don't really know" Ash said as he scratched the back of his head

"What do you mean you don't know?" Dawn asked

"Just that, I don't know. I mean I've been traveling for so long that I never really stopped to think about it" Ash said

What about Melody?" Misty asked

"Who's Melody?" Dawn asked curiously

"Oh, she's a girl we met in the Orange Islands. She gave Ash a kiss on the cheek when we landed on the island" Misty said

"Oh, so what about here?" Dawn asked

"No, I don't have a crush on her, besides I barely know her" Ash said

"Ash you don't have to really know someone to have a crush on them" Misty said

"Oh, okay" Ash said

Misty sighed, boy was Ash dense.

"Okay, what about Bianca?" Misty suggested

"Who's that?" Dawn asked her interested piqued again

"We met her in Altomare" Misty said

Dawn nodded

"She gave Ash a drawing and kissed him on the cheek too" Misty said

"Yeah, but we don't know if that was Bianca or Latias" Ash said

"Latias, where does Latias come into this?" Dawn asked

Ash and Misty then began to tell Dawn about their whole adventure in Altomare, though Ash told most of it and Misty just help fill in a few things.

"Oh okay, I understand now. Wow Ash! You sure have a lot of adventures" Dawn said

Ash shrugged his shoulders

"Okay, so do you have a crush on her?" Dawn asked

"No" his shook his head

Misty sighed, "Ash, there's got to be a girl you liked. I mean you've met a lot of them"

"I know Misty, but I wasn't really paying attention. I just wanted to get to my next gym battle" Ash said

Misty sighed again, but held her head. This wasn't going as well as they hoped.

"Come on Ash, there has to be a girl that caught your eye" Dawn said

Ash shook his head

"Sorry, but no one"

Dawn had a look on her face that said she wasn't going to give up.

"What comes to mind when I say May?" Dawn asked

Ash blinked

"Huh?"

"It's a simply question what comes to mind when May's name is said" Misty said

Ash leaned back in thought.

"Well I remember how new she was to Pokémon. She kind of reminded me of me when I started out. I didn't know much. But I didn't have the fear of Pokémon like she had though. But, anyway I decided to take her under my wing and teach her everything that I know about Pokémon. When she said she was going to be a coordinator instead of trainer I was the first to congratulate her. She was taking her first step in becoming independent. I watched her grow in front of my very eyes and I'm very proud to call her a friend" Ash said

"Wow Ash! I never thought you had such a way with words" Dawn said

Ash pulled his hat over his face to try to hide his red cheeks.

Misty enjoyed watching Ash acting all self-conscious because it was a rare sight to see.

"You seemed to like her Ash" Misty said

"Huh?"

"Yeah, the way you talked about her just now shows that you care deeply for her" Dawn said

"Of course I care for May. She's one of my best friends and we've been through a lot" Ash said

"Ash, you and I have been through a lot too and we've known each other longer than you and May. But do you really think you can say something about like you did May?" Misty asked

Ash was about to answer when he realized that this might be a trap. He grew quite smart and noticed a trap when he saw one.

"Ash, I'm not going to hurt you if you say no" Misty said

Ash was hesitant

"Oh just say it Ash" Dawn blurted out

"Fine, no I don't think I can say the same for you Mist. It's not that I don't appreciate everything you've done for me because I do, I really do. It just that it is different" Ash said

"I understand Ash, and thanks for being honest" Misty said

Ash nodded feeling a bit relieved

"So, we know you care a lot for May, this is great" Dawn squealed

Ash moved away from the squealing girl, afraid that the squealing might be contagious. Misty sighed and shook her head, could Dawn be anymore of a girl right now. Once Dawn was back in control of herself Ash moved back to his original position.

"What's going on here, why are you asking all these questions?" Ash asked

"Because, we want to know if you like May or not" Dawn said

Misty slapped her hand to her forehead as she sighed. Dawn can be so dumb sometimes.

"I don't get it, of course I like May, she's my best friend" Ash said confused

Misty again smacked her head with her hand. Her friend was so dense.

"What, what did I say?" Ash asked looking at Misty

"Ash, this whole thing was trying to get you to possible think of May in a more romantic way" Misty said since she was fed up

"Huh?"

Misty looked ready to throttle the young trainer when he was saved.

"Ash, there you are, where have you been?"

The three turned to find May standing at the gate to the backyard with her hands on her hips and looking a bit miffed.

"Hey May" Ash greeted

"Don't 'hey May' me. You were supposed to pick me up from the port, remember" May said seething slightly

Ash retreated back slightly

"It wasn't my fault I swear. Dawn and Misty made me lose track of time," the young trainer said

May set her eyes on the two girls that kept Ash from meeting her.

"We just wanted to talk to Ash, we had no idea he was supposed to meet you" Dawn said

Misty nodded

"Alright, come on Ash we should get going" May said

Ash nodded and got up.

"Where are you two going?" Dawn asked

"Just out, maybe we'll catch a movie or something" May said

"Like a date?" Dawn asked with excitement

May looked at Dawn with an odd look while Ash pulled his cap down to cover his face. Misty sighed.

"A date? Where in the world are you coming up with that Dawn?" May asked

Dawn began to explain herself and once she was finished May sighed.

"You have too much time on your hands Dawn. You should be spending that time training for your contests" May said wisely

Dawn looked down

"Come on Ash, let go" May said

Ash took May's arm and Dawn nearly squealed, but Misty covering the blue haired girl's mouth with her hand stopped it.

Ash and May were far away when they broke their silence.

"So those two were trying to get you to realize your feelings for me" May said

"Yeah" Ash said rubbing the back of his head

"When should we tell them?" May asked

"Soon" Ash answered

May pulled out a chain from around her neck and there was a sparkling diamond ring hanging from the chain. Ash had the help from the Oreburgh gym leader, Roark to excavate the diamond and shape it to fit the gold band Ash had chosen. The two got engaged when Ash went to Hoenn to see May. Ash first went to May's father Norman for permission and once he got it the young trainer took May out to a classy dinner and proposed to her as they took a nice walk in a nearby park. They kept this a secret since it was nice to have something just between the two of them.

"Yeah, soon sounds good to me" May said smiling

**End**

**A/N: that's the end of this one, I know that it is an odd way of ending it, but I couldn't think of another way of fitting the ending part in anywhere else. Thanks for reading and please review.**


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